ENZYMATIC-HYDROLYSIS IN ORGANIC-SOLVENTS FOR KINETIC RESOLUTION OF WATER-INSOLUBLE ALPHA-ACYLOXY ESTERS WITH IMMOBILIZED LIPASES

Authors
AKITA H UMEZAWA I MATSUKURA H
Citation
H. Akita et al., ENZYMATIC-HYDROLYSIS IN ORGANIC-SOLVENTS FOR KINETIC RESOLUTION OF WATER-INSOLUBLE ALPHA-ACYLOXY ESTERS WITH IMMOBILIZED LIPASES, Chemical and Pharmaceutical Bulletin, 45(2), 1997, pp. 272-278
Citations number
14
Categorie Soggetti
Pharmacology & Pharmacy",Chemistry
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
45
Issue
2
Year of publication
1997
Pages
272 - 278
Database
ISI
SICI code
0009-2363(1997)45:2<272:EIOFKR>2.0.ZU;2-1
Abstract
Enantioselective hydrolysis of water-insoluble alpha-acyloxy esters, ( +/-)-5 and (+/-)-6, was carried out using lipases immobilized with Cel ite or a synthetic prepolymer (ENTP-4000 or ENT-4000) in a water-satur ated organic solvent to produce chiral intermediates, (2S,3S)-5 and (2 S,3R)-4, for the synthesis of diltiazem hydrochloride 1 and (-)-indolm ycin 2, respectively, Furthermore, enantioselective hydrolysis of (+/- )-6 using lipid-lipase aggregates in water-saturated organic solvent w as also found to give (2S,3R)-4.